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Here's What To Expect

2,500 Beautiful Outlaw People. 5 Music Venues. Dozens of Unique Performances from over 30 Outlaw Country Artists. Multiple Memories to Last a Lifetime. One Unforgettable Experience on the Open Sea.

Calling all Outlaws! The Outlaw Country Cruise is back for its fifth voyage, sailing from Miami to Key West, Florida and Falmouth, Jamaica aboard the luxurious Norwegian Pearl. Join us January 29th to February 3rd, 2020 for an uncharted adventure brought to you by Sixthman and Renegade Circus. This 5-day odyssey on the high seas will be packed with distinctive performances, one of a kind collaborations, fun-filled activities with your fellow cruisers and some of your favorite artists, and so much more.

In addition to two days spent in beautiful ports, guests will enjoy a stacked lineup of Outlaw Country stars! This floating festival will host over 40 artists including The Mavericks, Lucinda Williams, Steve Earle & The Dukes, Kris Kristoferson & The Strangers, Ray Wylie Hubbard, Son Volt and so many more, performing shows in various configurations, including full band sets and “guitar pull” acoustic song swaps. You will also get to attend SiriusXM Sessions at Sea radio show tapings, hosted by SiriusXM Outlaw Country hosts, and Renegade Cinema film screenings and Q&A sessions. This wildly unique experience will provide unforgettable moments and incomparable memories that will last a lifetime.


All Aboard!

(Itinerary subject to change)

When booking flights we recommend that you arrive in Miami no later than 12:00pm, or in Ft. Lauderdale no later than 11:00am on January 29th. Return flights should be arranged to leave Miami after 12:00pm on February 3th, or leave Ft. Lauderdale after 1:00pm.

**Please allow additional time for customs clearance for international flights.


  • Wednesday, January 29
    Depart Port of Miami
    (approx. 3:30pm ET)
  • Thursday, January 30
    Key West, FL
    (8:00am to 3:30pm)
  • Friday, January 31
    Day At Sea
     
  • Saturday, February 1
    Falmouth, Jamaica
    (7:00am to 3:30pm)
  • Sunday, February 2
    Day At Sea
     
  • Monday, February 3
    Arrive Port of Miami
    (approx. 8:00am ET)

Ahoy, Vacation!

Key West

Key West

Thursday, January 30, 2020

Sunny weather, friendly people, and generous drinks make Key West an ideal port stop during The Outlaw Country Cruise! This tropical paradise has something for everyone. 

Known as the Southernmost Point, Key West is home to the only living coral barrier reef in the continental U.S. It is most notable for its laid back attitude and beautiful sunsets. Don't miss Duval Street, fresh seafood, margaritas, and water excursions. And be sure to treat yourself to the official dessert of the island city, key lime pie! 

Shore Excursions in Key West

Please note: Shore excursions will not be available until 4-6 weeks prior to sailing. You will be able to book an excursion once you have received your booking number.

Falmouth, Jamaica

Falmouth, Jamaica

Saturday, February 1, 2020

With white sandy beaches, crystal clear water and blue skies, it’s easy to relax in Jamaica. Aside from breathtaking beaches, Falmouth is also known for its 19th century Georgian architecture. The most popular dish on the island is cooked with jerk. Jerk, native to Jamaica, is a zesty mixture of spices that’s used as a rub to flavor meats, seafood and shellfish.

Shore Excursions in Falmouth, Jamaica

Please note: Shore excursions will not be available until 4-6 weeks prior to sailing. You will be able to book an excursion once you have received your booking number.

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